D Cyclopenthiazide C 561 Reference(s): US 2 520 015 (Eli Lilly; 1950; prior. 1948). Fomtulation(s): amp. 10 mg, 25 mg; sol. Trade Name(s): D: Copyronilum (Lil1y)- F: Cyclonarol (HCpatrol); I: Copyronil (Lilly); wfm comb.; wfm wfm USA: Clopane (Lilly); wfm Cyclopenthiazide (Cyclomethiazide) ATC: C03AA07 Use: diuretic, antihypertensive RN: 742-20-1 MF: C,3H,8C1N304S2 MW: 379.89 EINECS: 212-012-5 LD,,: 232 mglkg (M, i.v.1; >I gkg (M, p.0.); 142 mgkg (R, i.v.); 1 gfkg (R, p.0.) CN: 6-chloro-3-(cyclopentylmethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,l-dioxide Reference(s): BE 587 225 (Ciba; appl. 3.2.1960; USA-prior. 4.2.1959). Whitehead, C.W. et al.: J. Org. Chem. (JOCEAH) 26,2814 (1961). 6-amino-4-chloro- cyclopentyl- Formulation(s): tabl. 0.25 mg, 0.5 mg Cyclopenthiozide Tmde Name(s): D: Navidrex (Ciba); wfm Trasidrex (Novartis)-comb. USA: GB: Navidrex (Novartis) J: Navidrex (Ciba-Geigy- Navispare (Nova&)-comb. Takeda) 1,3-benrenedisulfamide acetaldehyde (cf. chlorothiozide synthesis) Navidrix (Ciba-Geigy); wfm Cyclopentobarbital ATC: NOSCA Use: hypnotic RN: 76-68-6 MF: C,,H,,N203 MW: 234.26 EINECS: 200-979-6 LDSa: 90 m@g (R, i.p.) CN: 5-(2-cyclopenten-1-yl)-5-(2-propeny1)-2,4,6(1H,3H,5H)-pyrimidinetrione H2C->Br , NoOC2H, + I ollyl bromide 0 3-bramo- diethyl diethyl Z-cyclo- cyclopentene molonate pentenylmolonote 562 C Cyclopentolate diethyl allyl- (2-cyclopenteny1)- urea malonote (I) Ryference(s): DRP 589 947 (Comp. de Bkthune; appl. 1930; F-prior. 1929). Trade Name(s): D: Cyclopal (Siegfried); wfrn Cyclopentolate ATC: SOIFAO4 Use: antispasmodic, mydriatic RN: 5 12- 15-2 MF: C,7H,,N03 MW: 291.39 EINECS: 208- 136-4 CN: a-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethy1amino)ethyl ester hydrochloride RN: 5870-29- 1 MF: C,,H2,N03 . HCI MW: 327.85 ETNECS: 227-521-8 LD,,,: 84 m&g (M, i.v.1; 960 mglkg (M, p.0.); >4 glkg (R, p.0.) H C CH 32 3.~g + $ isopropyl b OH brarnide 0 sodium phenyl- cyclo- acetate pentonone a-(1 -hydroxy- cyclopenty1)- phenylocetic acid (1) chloride 1 Cyclopentolate I Re;firence(s): US 2 554 51 1 (Schieffelin & Co.; 1951; prior. 1949) Formulation(s): eye drops 5 mg (0.5 %, 1 %) (as hydrochloride) Trade Name(s): D: Cyclopentolat GB: Minims Cyclopentolate Cyclomydril (A1con)- Augcntropfen (Alcon) (Chauvin) comb.; wfm Zyklolat ED0 (Mann) Mydrilate (Boehringer Ing.) generics and combinatio F: Skiacol (Alcon) 1: Ciclolux (Allergan) preparations; wfm USA: Cyclogyl (Alcon); wfrn Cyclophosphamide C 563 Cyclophosphamide ATC: LOlAAOl Use: antineoplastic RN: LD,,: CN: 50-1 8-0 MF: C,H,,Cl,N,O,P MW: 26 1 .O9 EINECS: 200-015-4 140 mglkg (M, i.v.); 137 mgkg (M, p.0.); 148 mgikg (R, i.v.); 160 rnglkg (R, p.0.) N,N-bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-arninc 2-oxide cn2 N(c2n5)3 v/ C', /? 4 POCI3f HN -+ P-N _____* % 1 % 3-amino- CI NH % I-proponol bis(2-chloro- N,N-bis-(2-chloro- Cyclophosphomide ethyl)omine ethy1)phosphor- ornidic dichloride Reference(s): DE 1 057 119 (ASTA-Werke; appl. 10.2.1956). US 3 018 302 (ASTA-Werke; 23.1.1962; D-prior. 10.2.1956). Formulation(s): drg. 50 mg; f. c. tabl. 50 rng; vial 100 mg, 200 rng. 500 mg, 1000 mg Trade Name(s): D: Cyclo-cell (cell pharrn) F: Endoxan ASTA (ASTA J: Endoxan (Shionogi) Cyclostln (Pharmacia & Medica) USA: Cytoxan (Bristol-Myers Upjohn) GB: Endoxana (ASTA Medica) Squibb) Endoxan (ASTA Medica I: Endoxan-Asta (ASTA AWD) Medica) Cycloserine (Orien tomy cin) ATC: J04AB01 Use: antibiotic (tuberculostatic) RN: 68-41-7 MF: C3H6N202 MW: 102.09 EINECS: 200-688-4 LD,,: 560 mgkg (M, i.~.); 5290 mg/kg (M, p.0.); >5 g/kg (R, p.0.); >2 g/kg (dog, p.o.1 CN: (R)-4-amino-3-isoxazolidinone hydrogen tartrate RN: 171 39-97-8 MF: C,H,N,O, , C,H606 MW: 252.18 from fermentation solutions of SLreptomyces garyphalus. 5. orchidoceus, 5. lovenduloe D-serine D-serine methyl ester hydrochloride 564 C Cyclothiazide 0 NH OH, OH- C140/CH3 "HCI + NH, hydroxylomine Rej'erence(s): a US 2 773 878 (Pfizer; 1956; appl. 1952). IJS 2 789 983 (Commercial Solvents; 1957; prior. 1954). IJS 2 845 433 (Merck & Co.; 1958; appl. 1955). b Plattner, P.A. et a].: Helv. Chim. Acta (HCACAV) 40, 1531 (1957). Smrt, J. et al.: Experientia (EXPEAM) 13, 291 (1957). alternative syntheses: US 2 772 280 (Merck & Co.; 1956; appl. 1954). US 2 840 565 (Merck & Co.; 1958; appl. 1954). Fornlulation(s): cps. 250 mg; tabl. 250 mg Trade Natne(s): D: D-Cycloserin "Roche" GB: Cycloscrine Roche Orient~nycin (Kayaku- (Roche); wfrn (Roche); wfm Kakeny aku) F: D-CyclosCrine Roche I: Ciclozer (Formulario Naz.) Serolnycin (Lilly- ' (Roche); wfm J: Cyclomycin (Shionogi) Schionogi) LISA: Seromycin (Dura) Cyclothiazide ATC: C03AA09 Use: diuretic RN: 2259-96-3 MF: C,4H16ClN,0,S, MW: 389.88 EINECS: 218-859-7 LDso: >5 g/kg (M, p.0.); >5 glkg (R, p.0.) CN: 3-bicyclo[2.2.l]hept-5-en-2-yl-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,l- dioxide OHC 'Ti CH2 ocrolein I + cyclo- bicycia[2.2. I]- pentodiene hept-5-ene-2- corboxaldehyde (I) P CI H 6-amino-4-chloro- Cyclothiozide 1.3-benrenedisulfomide (cf. chlorothiazide synthesis) Cyclovalone C 565 Referenceis): US 3 275 625 (Boehringer Ing.; 27.9.1966; prior. 23.1.1961). DE 1 125 938 (Thomae; appl. 12.2.1960). GB 915 236 (Eli Lilly; appl. 25.7.1961; USA-prior. 31.10.1960). Fomulation(s): tabl. 2.5 mg, 3 mg Trade Name(s): D: Dimapres (Dieckmannl- F: Cyclot6riam (Rous~el J: Valmiran (Boehringer- comb.; wfm Diamant)-comb. with Tanabe) triamterene USA: Anhydron (Lilly) C yclovalone Use: digestant, choleretic RN: 579-23-7 MF: C22H2205 MW: 366.41 EINECS: 209-438-9 LD,: 56 mglkg (M, i.v.) CN: 2,6-bis[(4-hydroxy-3-methoxyphenyl)methylene]cyclohexanone vanillin cyclo- I Cyclovolone hexanane Rejerence(s): AT 180 258 (A. v. Waldheim Chem. Pharm. Fabrik; appl. 1953). Rumpel, W.: Arch. Pharm. Ber. Dtsch. Pharm. Ges. (APBDAJ) 287, 350 (1 954). Fonnulation(s): gran. 0.661 100 g Trade Name(s): D: Beveno (Fischer); wfm F: Vanilone (16napharm) GB: Vanisorbyl (Nicholas); wfm Cycrimine ATC: NO4 Use: antiparkinsonian RN: 77-39-4 MF: C,,H,NO MW: 287.45 EINECS: 201-024-6 CN: a-cyclopentyl-a-phcnyl- 1 -piperidinepropanol hydrochloride RN: 126-02-3 MF: C,,H,,NO. HCl MW: 323.91 EINECS: 204-764-8 LDSo: 50 mgkg (M, i.v.); 349 mglkg (M, p.0.); 628 mg/kg (R, p.0.) MgBr ____, 0 cyclopentyl- magnesium aceto- paraform- piperidine phenone aldehyde propiophenone 566 C Cynarine Reference(s): IJS 2 680 115 (Winthrop-Steams, 1954; prior. 1949). Fonnulation(s): tabl. 0.25 mg, 0.5 mg Trade Nanze(s): I: Pagitane (Lilly); wfm USA: Pagitane (Lilly); wfm Cynarine ATC: A06AB20 Use: choleretic RN: 1 182-34-9 MF: C2,H2,0,, MW: 5 16.46 EINECS: 214-655-7 LD,,,: 1900 mg/kg (M, i.p.) CN: (la,3a,4a,5~)-1,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,5- dihydroxycyclohexanecarboxylic acid from Cynara scolymus (artichokes) leaves by extraction caffeic acid chloride 3.4-corbanyldioxy- cinnamic acid Reference(s): a US 2 863 909 (Farmitalia; 9.12.1958; I-prior. 28.5.1954). b US 3 100 224 (Farmitalia; 6.8.1963; I-prior. 28.5.1954). quinic acid synthesis of quinic acid lactone: Wolinsky, J. et al.: J. Org. Chern. (JOCEAH) 29, 3596 (1964). Cynarine Fornzulation(s): tabl y-lactone Trade Name(s): D: Benestan (Kar1spharma)- Listrocol (Carlo Erba); comb.; wfm wfm J: Methiocholin (Pfleger)- comb.; wfm Plemocil (Sumitomo) F Cyproheptadine C 567 Cyproheptadine ATC: R06AX02 Use: antiallergic, appetite stimulant RN: 129-03-3 MF: C,,H,,N MW: 287.41 EINECS: 204-928-9 LD,,; 15mgkg(M,i.v.); 106mglkg (M, p.0.); 295 mgtkg (R, p.0.) CN: 4-(SH-dibenzo[a,~cyclohepten-5-ylidene)-l-methylpiperidine hydrochIoride RN: 969-33-5 MF: C,,H,,N . HCI MW: 323.87 EINECS: 213-535-1 LD,,: 23 mgkg (M, i.v.);-69 &dkg (M , pa.); 295 mglkg (R, p.o.) HCI, CH,COOH, (cH3c0)20 ___) CH3 CH3 cyclohepten-5-one '33 4-chloro- 1-methyl piperidine Reference(s): US 3 014 91 1 (Merck & Co.; 26.12.1961; prior. 13.7.1959). Engelhardr, E.L. et al.: J. Med. Chem. (JMCMAR) 8, 829 (1965). Formulation(s): syrup 2 mg15 ml; tab]. 4 mg (as hydrochloride) Trade Name(s): D: Peritol (medphano) GB: Periactin (Merck Sharp & F: Pkriactine (Merck Sharp & Dohme) Dohme, as hydrochloride) I: Periactin (Neopharmed) J: Ifrasarl (Showa Shinyaku) ?? N I. CH3 Cyproheptodine Periactin (Merck-Ranyu) USA: Periactin (Merck; as hydrochloride) Cyproterone acetate ATC: L02BB; G03HB Use: antiandrogen RN: 427-5 1-0 MF: C2,H,7CI0, MW: 374.9 1 EINECS: 207-048-3 CN: (I p,2p)- I7-(acetyloxy)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-l,4,6-triene-3,20-dione cyproterone RN: 2098-66-0 MF: C2,H,CI03 MW: 374.91 0 + I chloronil 17-hydroxy- progesterone 568 C Cyproterone acetate 0 CH, H H methane 0 // Reference(s): DE 1 072 991 (Schering AG; appl. 25.10.1958). DE 1 096 353 (Schering AG; appl. 11.7.1959). DE 1 158 966 (Schering AG; appl. 29.4.1961). DE 1 189 991 (Schering AG; appl. 31.5.1963). HCI, CH COOH A, collidine. N2 1I1 3 CI US 3 234 093 (~chering AG; 872.1966; appl. 24.4.1962; D-prior. 29.4.1961). 0. CI Cyproterone acetate synthesis of 17-hydroxyprogesterone: DE 1 1 19 266 (Schering AG; appl. 18.12.1957). IJS 2 962 510 (Schering AG; 29.1 1.1960; appl. 9.12.1958; D-prior. 18.12.1957). alterr~ative syntlresis: DE 1 183 500 (Schering AG; appl. 12.10.1962). DOS 3 331 824 (Schering AG; appl. 1.9.1983). DOS 4 006 165 (Schering AG; appl. 25.2.1990). review: Wiechert, R.: Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys., Biol. (ZENBAX) 196,944 (1964). Fornlulation(s): amp. 300 mgi3 ml; tabl. 10 mg, 50 mg Trade Name(s): D: Androcur (Schering) ClimCne (Schering) Dianette (Schering)-comb. Climen (Schering)-comb. Diane (Schcring)-comb. I: Androcur (Schering) Diane (%hering)-comb. GB: Androcur (Schering) Diane (Schering)-comb. F: Androcur (Schering) Cyprostat (Schering) 1: Androcur (Schering) Cvtarabine C 569 Cytarabine (ara C; Cytosine arabinoside) ATC: LOlBCOl Use: antineoplastic, antiviral RN: 147-94-4 MF: CyH13N305 MW: 243.22 EINECS: 205-705-9 LDS& >7 gkg (M, i.v.); 3 150 mglkg (M, p.0.); >5 gkg (R, i.v.); >5 gkg (R, p.0.) CN: Camino- 1-P-D-arabinofuranosyl-2(1 H)-pyrimidinone monohydrochloride RN: 69-74-9 MF: CyH13N,0, . HCI LD,,: 826 mgkg (M, p.0.); >3.2 glkg (R, p.0.); 172 mgkg (dog, i.v.) 2.3.5-ti-0-benzyl- 2.4-dimethoxy- D-arabinofuranosyl pyrimidine chlon'de 1. NH, 2. H,, Pd-C I b Cytarabine I MW: 279.68 EINECS: 200-7 13-9 + Bn: P OH 0 CH3 I-j3-D-arabino- ocetic furanosyluracil anhydride 570 C Cytarabine Reference(s): NL-appl. 6 51 1 420 (Merck & Co.; appl. 1.9.1965; USA-prior. 2.9.1964). US 3 116 282 (Upjohn; 1963, prior. 1959). alternative synthesis: Roberts, W.K.; Dekker, C.A.: J. Org. Chern. (JOCEAH) 32, 816 (1967). Fromageot, H.P.M.; Reese, C.B.: Tetrahedron Lett. (TELEAY) 1966,3499. Claesen, C.A.A. et al.: Tetrahedron Lett. (TELEAY) 26,3859 (1985). Formulation(s): amp. 40 mg12 ml, 100 mg15 ml, 1 gl20 ml, 1 g110 ml Trade Name(s): D: Alexan (Mack) Cy tarbcl (RhBne-Poulenc ARA-cell (cell pharm) Roger Bellon) Udicil (Pharmacia & GB: Cytosar (Pharmacia & Upjohn) Upjohn) F: Aracytine (Pharmacia & I: Alexan (Byk Gulden) Upjohn) Aracytin (Upjohn) Erpalfa (Intes) J: Cyclocide (Nippon Shinyaku) Cytosar (Upjohn) USA: Cy tosar-U (Pharmacia & Upjohn) . RN: 225 9-9 6-3 MF: C,4H16ClN,0,S, MW: 389.88 EINECS: 21 8-8 5 9-7 LDso: >5 g/kg (M, p.0.); >5 glkg (R, p.0.) CN: 3-bicyclo[2.2.l]hept-5-en-2-yl-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide. N,N-bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-arninc 2-oxide cn2 N(c2n5)3 v/ C', /? 4 POCI3f HN -+ P-N _____* % 1 % 3-amino- CI NH % I-proponol bis(2-chloro- N,N-bis-(2-chloro- Cyclophosphomide. hypnotic RN: 7 6-6 8-6 MF: C,,H,,N203 MW: 234.26 EINECS: 20 0-9 7 9-6 LDSa: 90 m@g (R, i.p.) CN: 5-( 2-cyclopenten-1-yl )-5 -( 2-propeny1 )-2 ,4,6(1H,3H,5H)-pyrimidinetrione H2C->Br , NoOC2H,